1-Bromooctadecane → 15-Octadecyl-7,15-diazadispiro[5.1.5~8~.3~6~]hexadecane-14,16-dione

HRID 2072289Notes

Reaction equation

HRID 2072289 reaction equation
[CH2:1]1[C:6]2([C:16](=[O:17])[NH:15][C:14](=[O:18])[C:8]3([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].[CH2:21](Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>CO.CN(C=O)C.CCOCC>[CH2:38]([N:15]1[C:16](=[O:17])[C:6]2([CH2:5][CH2:4][CH2:3][CH2:2][CH2:1]2)[NH:7][C:8]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[C:14]1=[O:18])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH3:21]

Participants

7

Reactant 3

HCID 82181-BromooctadecaneHCID 14797Potassium HydroxideHCID 122347397,15-Diazadispiro[5.1.5.3]hexadecane-14,16-dione

Product 1

HCID 1853367615-Octadecyl-7,15-diazadispiro[5.1.5~8~.3~6~]hexadecane-14,16-dione

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 10.0 g. (0.04 moles) of 7,15-diazadispiro [5,1,5,3] hexadecane-14,16-dione in 150 ml of anhydrous methanol in a 500 ml flask was added 2.6 g. of 86% KOH (0.04 moles) and the mixture was shaken until solution was obtained. The reaction mixture was then evaporated to dryness under reduced pressure. The residue was transferred to a 300 ml 3-necked flask equipped with a stirrer, thermometer, condenser with drying tube, dropping funnel and nitrogen inlet with the aid of a small amount of dry DMF. To the potassium imide salt, under a nitrogen atmosphere, was added 150 ml of dry DMF. To the stirred solution was added dropwise a solution of 13.3 g. (0.04 moles) of n-octadecyl bromide in 50 ml of DMF. The reaction mixture was heated slowly to 75° C and held at that temperature for 3 hours. The reaction mixture was cooled and allowed to stand at room temperature overnight. The reaction mixture was then taken up in 500 ml ether, the ether solution washed well with water, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue, which crystallized on standing, was recrystallized from methanol yielding 14.3 g. of white needles as the product, m.p. 39°-40° C.

Workup

  1. customwas obtained
  2. customThe reaction mixture was then evaporated to dryness under reduced pressure
  3. customThe residue was transferred to a 300 ml 3-necked flask
  4. customequipped with a stirrer
  5. customthermometer, condenser with drying tube
  6. additionTo the potassium imide salt, under a nitrogen atmosphere, was added 150 ml of dry DMF
  7. additionTo the stirred solution was added dropwise a solution of 13.3 g
  8. temperatureThe reaction mixture was cooled
  9. waitto stand at room temperature overnight
  10. washthe ether solution washed well with water
  11. dry with materialdried over anhydrous Na2SO4
  12. customevaporated under reduced pressure
  13. customThe residue, which crystallized
  14. customwas recrystallized from methanol yielding 14.3 g

Sources & evidence

ORD record
ord-60d655f2283d4f5bb43e03d1f9327f69
Source dataset
uspto-grants-1977_09
Patent number
US04051137

Reaction notes

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